CA2330756C - Indole derivatives and their use for the treatment of malignant and other diseases based on pathological cell proliferation - Google Patents

Indole derivatives and their use for the treatment of malignant and other diseases based on pathological cell proliferation Download PDF

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Publication number
CA2330756C
CA2330756C CA002330756A CA2330756A CA2330756C CA 2330756 C CA2330756 C CA 2330756C CA 002330756 A CA002330756 A CA 002330756A CA 2330756 A CA2330756 A CA 2330756A CA 2330756 C CA2330756 C CA 2330756C
Authority
CA
Canada
Prior art keywords
indolyl
general formula
radical
compound
dihydro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA002330756A
Other languages
English (en)
French (fr)
Other versions
CA2330756A1 (en
Inventor
Siavosh Mahboobi
Sabine Kuhr
Herwig Pongratz
Alfred Popp
Harald Hufsky
Frank-D. Bohmer
Steffen Teller
Andrea Uecker
Thomas Beckers
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aeterna Zentaris GmbH
Original Assignee
Zentaris AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19838506A external-priority patent/DE19838506C2/de
Application filed by Zentaris AG filed Critical Zentaris AG
Priority to CA002496859A priority Critical patent/CA2496859A1/en
Publication of CA2330756A1 publication Critical patent/CA2330756A1/en
Application granted granted Critical
Publication of CA2330756C publication Critical patent/CA2330756C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • A61P5/04—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/56—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Endocrinology (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Saccharide Compounds (AREA)
CA002330756A 1998-05-04 1999-04-22 Indole derivatives and their use for the treatment of malignant and other diseases based on pathological cell proliferation Expired - Fee Related CA2330756C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002496859A CA2496859A1 (en) 1998-05-04 1999-04-22 Indole derivatives and their use for the treatment of malignant and other diseases based on pathological cell proliferation

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19819835 1998-05-04
DE19838506.4 1998-08-25
DE19819835.3 1998-08-25
DE19838506A DE19838506C2 (de) 1998-05-04 1998-08-25 Indolderivate und deren Verwendung zur Behandlung von malignen und anderen, auf pathologischen Zellproliferationen beruhenden Erkrankungen
PCT/DE1999/001214 WO1999057117A2 (de) 1998-05-04 1999-04-22 Indolderivate und deren verwendung zur behandlung von malignen und anderen, auf pathologischen zellproliferationen beruhenden erkrankungen

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002496859A Division CA2496859A1 (en) 1998-05-04 1999-04-22 Indole derivatives and their use for the treatment of malignant and other diseases based on pathological cell proliferation

Publications (2)

Publication Number Publication Date
CA2330756A1 CA2330756A1 (en) 1999-11-11
CA2330756C true CA2330756C (en) 2007-10-02

Family

ID=26045937

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002330756A Expired - Fee Related CA2330756C (en) 1998-05-04 1999-04-22 Indole derivatives and their use for the treatment of malignant and other diseases based on pathological cell proliferation

Country Status (22)

Country Link
US (2) US6407102B1 (no)
EP (1) EP1109785B1 (no)
JP (1) JP2002514572A (no)
CN (1) CN1151127C (no)
AT (1) ATE230394T1 (no)
AU (1) AU752464B2 (no)
BG (1) BG104996A (no)
BR (1) BR9911017A (no)
CA (1) CA2330756C (no)
CZ (1) CZ20003960A3 (no)
DE (1) DE59903921D1 (no)
DK (1) DK1109785T3 (no)
ES (1) ES2190221T3 (no)
HK (1) HK1038354A1 (no)
HU (1) HUP0102563A3 (no)
IL (1) IL139056A0 (no)
NO (1) NO317261B1 (no)
NZ (1) NZ507735A (no)
PL (1) PL346840A1 (no)
SK (1) SK16352000A3 (no)
TR (1) TR200003206T2 (no)
WO (1) WO1999057117A2 (no)

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SK16352000A3 (sk) 1998-05-04 2002-07-02 Zentaris Ag Indolové deriváty, spôsob ich výroby, ich použitie na liečivá obsahujúce tieto zlúčeniny
US6719520B2 (en) 1998-10-08 2004-04-13 Smithkline Beecham Corporation Method and compounds
JP2002527419A (ja) * 1998-10-08 2002-08-27 スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー Ｇｓｋ−３阻害物質としてのピロール−２，５−ジオン類
WO2002000641A2 (en) * 2000-06-28 2002-01-03 Eli Lilly And Company Spla2 inhibitors
AU2001275794A1 (en) 2000-07-28 2002-02-13 Sumitomo Pharmaceuticals Co. Ltd. Pyrrole derivatives
TW557298B (en) * 2000-08-14 2003-10-11 Ciba Sc Holding Ag A compound, a photopolymerizible composition, a process for producing coatings and a method for causing a photoinitiator to accumulate at the surface of coatings
US20030032625A1 (en) * 2001-03-29 2003-02-13 Topo Target Aps Succinimide and maleimide derivatives and their use as topoisomerase II catalytic inhibitors
DE10143079A1 (de) * 2001-09-03 2003-05-15 Zentaris Ag Cyclische Indol- und Heteroindolderivate, deren Herstellung und Verwendung als Arzneimittel
US20050267303A1 (en) * 2001-09-04 2005-12-01 Zentaris Ag Cyclic indole and heteroindole derivatives and methods for making and using as pharmaceuticals
EP1479384A1 (en) * 2002-01-30 2004-11-24 Sumitomo Pharmaceuticals Company, Limited Fibrosis inhibitor
US6800655B2 (en) 2002-08-20 2004-10-05 Sri International Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
US7098231B2 (en) 2003-01-22 2006-08-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US7223785B2 (en) 2003-01-22 2007-05-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
CA2565387A1 (en) * 2004-05-03 2005-11-17 Ilypsa, Inc. Modulation of lysophosphatidylcholine and treatment of diet-induced conditions
CA2627043A1 (en) * 2005-11-03 2007-05-18 Ilypsa, Inc. Multivalent indole compounds and use thereof as phospholipase-a2 inhibitors
US20090318492A1 (en) * 2005-11-03 2009-12-24 Han-Ting Chang Indole compounds having c4-acidic substituents and use thereof as phospholipase-a2 inhibitors
WO2007056184A2 (en) * 2005-11-03 2007-05-18 Ilypsa, Inc. Azaindole compounds and use thereof as phospholipase-a2 inhibitors
US20070135383A1 (en) * 2005-11-03 2007-06-14 Han-Ting Chang Phospholipase inhibitors, including multi-valent phospholipase inhibitors, and use thereof, including as lumen-localized phospholipase inhibitors
US20090306171A1 (en) * 2005-11-03 2009-12-10 Han-Ting Chang Indole compounds having c4-amide substituents and use thereof as phospholipase-a2 inhibitors
US20090142832A1 (en) * 2007-11-29 2009-06-04 James Dalton Indoles, Derivatives, and Analogs Thereof and Uses Therefor
SI2448938T1 (sl) 2009-06-29 2014-08-29 Incyte Corporation Experimental Station Pirimidinoni kot zaviralci pi3k
CN101704828A (zh) * 2009-11-04 2010-05-12 中国科学院昆明植物研究所 山橙素类双吲哚化合物,其药物组合物及其制备方法和用途
WO2011075643A1 (en) * 2009-12-18 2011-06-23 Incyte Corporation Substituted heteroaryl fused derivatives as pi3k inhibitors
TW201130842A (en) * 2009-12-18 2011-09-16 Incyte Corp Substituted fused aryl and heteroaryl derivatives as PI3K inhibitors
US9193721B2 (en) 2010-04-14 2015-11-24 Incyte Holdings Corporation Fused derivatives as PI3Kδ inhibitors
US9062055B2 (en) 2010-06-21 2015-06-23 Incyte Corporation Fused pyrrole derivatives as PI3K inhibitors
ES2764848T3 (es) 2010-12-20 2020-06-04 Incyte Holdings Corp N-(1-(fenilo sustituido)etilo)-9H-purina-6-aminas como inhibidores de PI3K
US9108984B2 (en) 2011-03-14 2015-08-18 Incyte Corporation Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors
WO2012135009A1 (en) 2011-03-25 2012-10-04 Incyte Corporation Pyrimidine-4,6-diamine derivatives as pi3k inhibitors
HUE030869T2 (en) 2011-09-02 2017-06-28 Incyte Holdings Corp Heterocyclic amines as inhibitors of PI3K
AR090548A1 (es) 2012-04-02 2014-11-19 Incyte Corp Azaheterociclobencilaminas biciclicas como inhibidores de pi3k
WO2015191677A1 (en) 2014-06-11 2015-12-17 Incyte Corporation Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors
TWI748941B (zh) 2015-02-27 2021-12-11 美商英塞特公司 Ｐｉ３ｋ抑制劑之鹽及製備方法
WO2016183060A1 (en) 2015-05-11 2016-11-17 Incyte Corporation Process for the synthesis of a phosphoinositide 3-kinase inhibitor
WO2016183063A1 (en) 2015-05-11 2016-11-17 Incyte Corporation Crystalline forms of a pi3k inhibitor
CN106317169B (zh) * 2015-06-23 2019-07-02 首都医科大学 双吲哚-二肽衍生物,其合成,抗血栓活性和制备抗血栓剂的应用
CN109790191B (zh) * 2016-08-05 2022-04-08 香港大学 铂配合物及其使用方法
CN114364798A (zh) 2019-03-21 2022-04-15 欧恩科斯欧公司 用于治疗癌症的Dbait分子与激酶抑制剂的组合
WO2020245208A1 (en) 2019-06-04 2020-12-10 INSERM (Institut National de la Santé et de la Recherche Médicale) Use of cd9 as a biomarker and as a biotarget in glomerulonephritis or glomerulosclerosis
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Also Published As

Publication number Publication date
WO1999057117A3 (de) 2001-04-12
IL139056A0 (en) 2001-11-25
DE59903921D1 (de) 2003-02-06
CN1310705A (zh) 2001-08-29
DK1109785T3 (da) 2003-04-22
US6407102B1 (en) 2002-06-18
HK1038354A1 (en) 2002-03-15
EP1109785A2 (de) 2001-06-27
CZ20003960A3 (cs) 2002-04-17
TR200003206T2 (tr) 2001-07-23
ATE230394T1 (de) 2003-01-15
NZ507735A (en) 2003-04-29
US20030008898A1 (en) 2003-01-09
HUP0102563A2 (hu) 2001-11-28
PL346840A1 (en) 2002-02-25
AU752464B2 (en) 2002-09-19
WO1999057117A2 (de) 1999-11-11
CN1151127C (zh) 2004-05-26
NO317261B1 (no) 2004-09-27
EP1109785B1 (de) 2003-01-02
US6812243B2 (en) 2004-11-02
AU4497599A (en) 1999-11-23
BR9911017A (pt) 2001-02-06
NO20005448L (no) 2000-10-27
ES2190221T3 (es) 2003-07-16
NO20005448D0 (no) 2000-10-27
BG104996A (en) 2001-07-31
CA2330756A1 (en) 1999-11-11
HUP0102563A3 (en) 2003-04-28
SK16352000A3 (sk) 2002-07-02
JP2002514572A (ja) 2002-05-21

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